1,3-Dipropyl-8-(4-sulfophenyl)xanthine → XANTHINE13DIPROPYL84DIMETHYLAMINOETHYLAMINOSULFO

HRID 1262528Notes

Reaction equation

HRID 1262528 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:19]=[CH:18][C:17]([S:20](O)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH2:25][CH3:26])[C:5]1=[O:27])[CH2:2][CH3:3].S(Cl)(Cl)=O.[CH3:32][N:33]([CH2:35][CH2:36][NH2:37])[CH3:34]>CN(C)C=O>[CH3:32][N:33]([CH3:34])[CH2:35][CH2:36][NH:37][S:20]([C:17]1[CH:18]=[CH:19][C:14]([C:9]2[NH:10][C:11]3[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:27])[N:6]([CH2:24][CH2:25][CH3:26])[C:7]=3[N:8]=2)=[CH:15][CH:16]=1)(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 13301,3-Dipropyl-8-(4-sulfophenyl)xanthineHCID 24386Thionyl ChlorideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 15587312XANTHINE13DIPROPYL84DIMETHYLAMINOETHYLAMINOSULFOYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(1,3-dipropyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid (3.93 g, 0.01 moles) and N,N-dimethylformamide (100 ml) is prepared, cooled to 0° C., treated with thionyl chloride (2.4 g, 0.02 moles), and permitted to warm to ambient temperature with vigorous stirring. The resulting slurry is cooled to 0° C., treated with a solution of unsym dimethylethylenediamine (8.8 g, 0.10 mole) in N,N-dimethylformamide (11 ml) added in one portion, and allowed to warm to ambient temperature. The resulting solution is concentrated on a rotary evaporator. The residue is suspended in water, filtered, recrystallized from ethanol, and dried at 78° to yield 0.60 grams of N-[2-(dimethylamino)ethyl]-4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)benzenesulfonamide, mp, 270°-272° C.(d).

Workup

  1. customis prepared
  2. temperatureto warm to ambient temperature with vigorous stirring
  3. temperatureThe resulting slurry is cooled to 0° C.
  4. additionadded in one portion
  5. temperatureto warm to ambient temperature
  6. concentrationThe resulting solution is concentrated on a rotary evaporator
  7. filtrationfiltered
  8. customrecrystallized from ethanol
  9. customdried at 78°

Sources & evidence

ORD record
ord-6cb7e8a524624686af6f5ec3c100e33f
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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